CH311660A

CH311660A - Process for the production of a new basic substituted fatty acid amide.

Info

Publication number: CH311660A
Authority: CH
Inventors: Aktiengesellschaft Cilag
Original assignee: Cilag Ag
Priority date: 1952-06-08
Filing date: 1952-06-08
Publication date: 1955-11-30

Description

  

  



  Verfahren zur Herstellung eines neuen basisch substituierten   Fettsäureamides.   



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen   basiseli    substituierten FettsÏureamides, welehes dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1     
 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin umsetzt.



   Der   Rest X kann    in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie zum Beispiel einer Al   kvlsulíonvloxy oder Arylsulfonyloxygruppe,    bestehen. Der Austausch der Gruppe X gegen den Diäthylaminorest erfolgt zum Beispiel durch einfaches Erwärmen mit   Diäthylamins    gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels oder von Diäthylamin im Überschuss. Das DiÏthyl   a minoessigsäure-N- (3-o-methoxy-phenoxy-pro-      pyl-2)-isopropylamid    ist ein   farbloses, vnter    0, 02 mm bei   147-148  siedendes ol.   



   Das neue Amid soll als   Lokalanästhetikum    und als Zwisehenprodukt zur Herstellung weiterer Derivate Verwendung finden.



   Beispiel :
28, 3 g Chloressigsäure-N-   (3-o-methoxy-      phenoxy-propyl-2)-isopropylamid lmd    15, 0 g Diäthylamin werden zusammen in 200   em3    abs. Benzol 2 Stunden auf dem Wasserbad erhitzt. Das Reaktionsgemisch wird mit Wasser ausgeschüttelt und dann mit 2n-Salzsäure ausgezogen. Darauf wird der salzsaure Auszug mit Ather extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt und das ausgeschiedene   il    in   Ather    aufgenommen. Nach dem Trocknen der ¯therausz ge über Pottasche wird der Äther verdampft und der   Rückstand    im Hochvakuum destilliert.



   Dabei gewinnt man das unter 0, 02 mm bei 147-148  siedende Diäthylaminoessigsäure N- (3-o-methoxy-phenoxy-propyl-2)-isopropylamid in guter Ausbeute. Farbloses   öl,    schwer   löslieh    in Wasser, gut in organischen   Losungs-    mitteln und in verdünnten Mineralsäuren.  



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbin  dung    der Formel
EMI1.2     
 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  Process for the production of a new basic substituted fatty acid amide.



   The subject of the present patent forms a process for the production of a new basiseli substituted FettsÏureamides, which is characterized in that a compound of the formula
EMI1.1
 in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine.



   The radical X can consist of a halogen atom or some other reactive substituent suitable for replacement with the basic radical, such as, for example, an Al kvlsulíonvloxy or arylsulphonyloxy group. Group X is exchanged for the diethylamino radical, for example, by simply heating with diethylamine, if appropriate in the presence of a basic condensing agent or of excess diethylamine. Diethylaminoacetic acid-N- (3-o-methoxyphenoxy-propyl-2) -isopropylamide is a colorless oil that boils below 0.02 mm at 147-148.



   The new amide is to be used as a local anesthetic and as an intermediate product for the manufacture of further derivatives.



   Example:
28.3 g of chloroacetic acid-N- (3-o-methoxyphenoxy-propyl-2) -isopropylamide and 15.0 g of diethylamine are mixed together in 200 em3 abs. Benzene heated on a water bath for 2 hours. The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid. Then the hydrochloric acid extract is extracted with ether, with ice cooling with conc. Sodium hydroxide solution was added and the separated oil was taken up in ether. After drying the extracts over potash, the ether is evaporated and the residue is distilled in a high vacuum.



   The diethylaminoacetic acid N- (3-o-methoxy-phenoxy-propyl-2) -isopropylamide, boiling below 0.02 mm at 147-148, is obtained in good yield. Colorless oil, poorly soluble in water, good in organic solvents and in dilute mineral acids.



   PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid amide, characterized in that a compound of the formula
EMI1.2
 

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims

** WARNING ** Beginning of CLMS field could overlap end of DESC **.

Process for the production of a new basic substituted fatty acid amide.

The subject of the present patent forms a process for the production of a new basiseli substituted FettsÏureamides, which is characterized in that a compound of the formula EMI1.1 in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine.

The radical X can consist of a halogen atom or some other reactive substituent suitable for replacement with the basic radical, such as, for example, an Al kvlsulíonvloxy or arylsulphonyloxy group. Group X is exchanged for the diethylamino radical, for example, by simply heating with diethylamine, if appropriate in the presence of a basic condensing agent or of excess diethylamine. Diethylaminoacetic acid-N- (3-o-methoxyphenoxy-propyl-2) -isopropylamide is a colorless oil that boils below 0.02 mm at 147-148.

The new amide is to be used as a local anesthetic and as an intermediate product for the manufacture of further derivatives.

Example: 28.3 g of chloroacetic acid-N- (3-o-methoxyphenoxy-propyl-2) -isopropylamide and 15.0 g of diethylamine are mixed together in 200 em3 abs. Benzene heated on a water bath for 2 hours. The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid. Then the hydrochloric acid extract is extracted with ether, with ice cooling with conc. Sodium hydroxide solution was added and the separated oil was taken up in ether. After drying the extracts over potash, the ether is evaporated and the residue is distilled in a high vacuum.

The diethylaminoacetic acid N- (3-o-methoxy-phenoxy-propyl-2) -isopropylamide, boiling below 0.02 mm at 147-148, is obtained in good yield. Colorless oil, poorly soluble in water, good in organic solvents and in dilute mineral acids.

PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid amide, characterized in that a compound of the formula EMI1.2 in which X is a reactive radical which is split off during the reaction, is reacted with diithylamine. The diethylaminoacetic acid-N- (3-o-methoxy .. phenoxy-propyl-2) -isopropylamide obtained in this way forms a colorless, below 0.02 mm boiling at 147-148 (il.

The new amide will be used as a local anesthetic and as an intermediate product.

SUBClaim: Process according to patent claim, characterized in that a haloacetic acid-N- (3-o-methoxy-phenoxy-propyl-2) -isopropylamide is allowed to react with diethylamine.